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317 Dyer Rd, Sharon
$699,000
3 Beds ⋅ 4 Baths ⋅ 5110925 MLS
The property with a little something for everyone! Picture waking up to sweeping views over a roughly ~6.5 acre meadow, occasionally dotted with friendly grazing horses from next door for an extra dose of charm. Whether you dream of raising animals, starting a hobby farm, or just want room to roam, the big barn with adjustable stalls is ready and waiting for whatever you have in mind. The house is just as versatile as the land around it. A durable standing seam metal roof tops a two car garage with an in-law suite above it, plus a mudroom that offers enough privacy to allow that bonus space to double as a small rental or a cozy retreat for guests. There's no shortage of places to unwind or entertain, from the living room and family room to the sunroom, screened porch, and a finished room in the basement. Upstairs above the main living area you'll find three bedrooms, including one with its own en-suite bathroom, while the other two share a second full bath. Life out here feels wonderfully quiet, yet you're only about 3 miles from Exit 2 on I-89, keeping your commute simple no matter where you're headed. There is also the bonus of high school choice alongside Sharon's own schools. Come see for yourself what makes this place special. Reach out today to schedule a showing!

317 Dyer Rd, Sharon

Listing courtesy of Holly Hall from Hall Collins Real Estate Group. ()
32 Calkinstown Rd, Sharon
$650,000
3 Beds ⋅ 3 Baths ⋅ 24208108 MLS
Enchanting circa-1850 cedar-shingled cottage tucked into a lush, beautifully landscaped setting along one of Sharon's picturesque country roads. Surrounded by mature specimen trees, layered perennial gardens, stone walls and pathways, and a meandering brook, the property offers a wonderful sense of privacy and the feeling of a secluded garden retreat. Inside, the home is warm and inviting, with original exposed beams that speak to its 19th-century character. A spacious eat-in country kitchen offers an inviting gathering place. The generously proportioned living room features 10-foot ceilings and a fireplace. The home offers three bedrooms and two-and-a-half baths, including a main-floor primary bedroom with an ensuite bath. Two porches, including a screened in porch, are a highlight of the property, extending the living spaces outdoors and creating idyllic settings for seasonal dining, entertaining, morning coffee, or quiet evenings overlooking the gardens. A separate barn currently serves as a two-car garage and offers additional possibilities for studio, workshop, or other creative use. The house also has a newly installed generator. Rich in character and beautifully connected to its natural surroundings, this charming country cottage captures the essence of relaxed Litchfield County living, all just minutes from the center of Sharon. Bring your vision and make it your own.

32 Calkinstown Rd, Sharon

Listing courtesy of Julie Einhorn from Compass Connecticut, LLC. (347) 853-1426 (203) 293-9715
494 Eastman Rd, Sharon
$375,000
3 Beds ⋅ 3 Baths ⋅ 5110125 MLS
This Sharon Vermont home has been renewed by its current owner with many thoughtful updates including hardwood floors, remodeled bathrooms, and a new heating system and oil tank since purchasing to name a few. There are still a few updates that can be made but the home is move in ready and is eager to house the next occupants. There are seasonal westerly views once the autumn leaves fall from their branches but since it appears you have control of the trees, a year round view may be possible. And let me tell you, it's spectacular with the setting sun backdropped against the valley and mountain setting. Did I say sun? Part of what this owner loved about this home was how much natural light it gets! Three large bedrooms await slumbering heads. Open kitchen to dining or kitchen to living if you desire seems great for entertaining. The exterior deck, with a little additional support, is great for entertaining and provides access to the back and side yards. Is this the one for you?

494 Eastman Rd, Sharon

Listing courtesy of Leila Tarantelli from KW Coastal and Lakes & Mountains Realty/Hanover. ()
31 Madison Ave, Sharon
$648,500
3 Beds ⋅ 2 Baths ⋅ 73577455 MLS
9/27 OPEN HOSUE CANCELED! UNBEATABLE VALUE! Gracious 3 Bed, 1.5 Bath mid-century, multi-level home on approx. 1 acre of land in desirable Sharon neighborhood! Offered for the first time, this home features hardwood floors and mechanical updates throughout, including brand new septic system (to be installed at seller's expense), newer boiler/tankless HW heater, and 2017 architectural shingle roof. First floor offers kitchen with SS appliances open to large dining/family room, 1/2 bath and laundry room, and sliders out to 3-season porch and yard. Second level features expansive fireplaced living room with 11' vaulted ceilings and natural light throughout. Top floor has three generous bedrooms with ample closet space, and full bath with tub. Walkout lower level is heated, and would make a great family room, playroom, or office space. Large lot with ample privacy, carport, and mature plantings and trees. Close to Cobbs Corner shops/restaurants, commuter rail, and walking distance to Crescent Ridge! Move right in, or add your cosmetic touches to this great home!

31 Madison Ave, Sharon

Listing courtesy of Listing Agent: Seth Mitchell from Listing Office: The Mitchell Group.
10 Suffolk Rd, Sharon
$650,000
3 Beds ⋅ 1 Baths ⋅ 73576471 MLS
Some homes give you more than the numbers suggest—and 10 Suffolk is one of them. Tucked onto a quiet Sharon neighborhood street, this charming 3-bedroom Cape delivers the spaces you need, the backyard you’ve been hoping for, and a location that makes everyday life just a little easier.Step inside to a bright, welcoming main level where hardwood floors flow through a sun-filled living room, dining room and updated kitchen with stainless appliances, stone counters and tile backsplash. Just beyond the kitchen, the deck becomes an extension of the home—overlooking a patio and spacious, newly fenced backyard made for morning coffee, summer dinners, four-legged friends, and weekends outside.A first-floor bedroom and full bath offer rare flexibility for one-level living, guests or a home office, while two additional bedrooms upstairs create private retreats away from the main living spaces.And then there’s the lower level—because this home lives much bigger than you’d expect. A finished family room is ready for movie nights, game days or a second living area, while an additional bonus room gives you options for a home office, gym, playroom, hobby space or guest overflow. Its tucked-away location also makes it an especially great fit for overnight guests, or anyone working nontraditional hours who appreciates a quieter, darker space for daytime sleep. There’s also basement laundry, storage, interior access, and space for a workshop!Central air, an attached 1-car garage, and thoughtful improvements add everyday comfort, including a new backyard fence and Mass Save–coordinated blown-in insulation added to attic areas. Major updates include FENCE (2024); MASS SAVE (2024); ROOF (2017); SIDING (2017); WINDOWS (2017); OIL TANK (2017); GARAGE DOOR (2017); APPLIANCES (2017); HOT WATER TANK (2017)But perhaps the best feature is the one you can’t renovate: Sharon. Enjoy convenient access to schools, commuter rail, Lake Massapoag, outdoor recreation, shopping and major routes—all while coming home to your own private backyard, and home with thoughtfully curated moments sure to check all of your boxes and needs!10 Suffolk isn’t about having more house than you need. It’s about having the right spaces, in the right town, with room for real life to happen. Welcome home!

10 Suffolk Rd, Sharon

Listing courtesy of Listing Agent: The Real Estate Ladies Team from Listing Office: REMAX Executive Realty.
455 Turnpike Rd, Sharon
$399,000
3 Beds ⋅ 2 Baths ⋅ 5109135 MLS
WOW! Picture-perfect, completely updated and ready to impress! This dreamy ranch has been transformed inside and out with stylish, modern finishes throughout and is set on a beautiful 2 acre lot. From the stunning front entrance to the exceptional outdoor living space, this is a home that immediately catches your eye and continues to impress. The open-concept kitchen, dining and living area is the centerpiece, featuring cathedral ceilings, recessed lighting and a beautifully appointed, fully applianced kitchen. The primary suite is equally impressive, with its own cathedral ceiling accented by exposed beams, a spacious walk-in closet and private bath with a gorgeous walk-in shower. Two additional bedrooms and a second full bath complete the main level. The full basement provides abundant space for storage, a workshop, hobbies and more. Outside, you'll love the beautifully designed front entrance and walkway, plenty of parking and the spectacular 18' x 18' stamped-concrete patio - perfect for relaxing, entertaining and enjoying the private 2-acre setting. Whether you're purchasing your first home, looking to downsize, or simply want the convenience of single-floor living, this property checks all the boxes. Opportunities to own a completely updated, HGTV-style home with this level of appeal are rare. Don't miss this one!

455 Turnpike Rd, Sharon

Listing courtesy of Cory Gracie from LAER Realty Partners. ()
12 Summer Street, Sharon
$700,000
3 Beds ⋅ 2 Baths ⋅ 73573480 MLS
Discover the perfect blend of charm, convenience, and location in the heart of Sharon! Ideally situated in a Center of Town location, this home is just moments from the commuter rail service to Boston and Providence, award-winning schools, parks, playgrounds, and the scenic shores of Lake Massapoag. Step inside to a bright and sun-filled living room that flows effortlessly into the dining area and updated country kitchen with QUARTZ counters and MAPLE cabinets. Upstairs, you will find three good size bedrooms, along with the updated full bath. The versatile walk-out lower level provides exceptional flexibility for guests, remote work, multigenerational living and plenty of storage space. Set on a generous quarter-acre lot, there is plenty of space to play, garden, entertain, or simply relax and enjoy the peaceful surroundings on the deck. Don't miss this wonderful opportunity to enjoy all that Sharon has to offer from an unbeatable in-town location!

12 Summer Street, Sharon

Listing courtesy of Listing Agent: Seth Stollman from Listing Office: Keller Williams Elite - Sharon.
190 Cornwall Bridge Rd, Sharon
$635,000
3 Beds ⋅ 3 Baths ⋅ 24201544 MLS
Set on two private acres just minutes from the village of Sharon, this inviting Colonial offers a wonderful blend of country privacy and everyday convenience. The main level features a spacious open-concept kitchen, living room, and dining area, complemented by a separate family room or home office. A whole-house media surround sound system enhances the living spaces throughout and an attached two-car garage provides added convenience. Upstairs, the generous primary suite offers multiple closets, including a walk-in, and a full bath with double vanity. Two additional bedrooms share a second full bath. The finished lower level provides flexible space for a recreation room, home gym, media room, or additional living area. Outside, a private back patio with a shade pergola creates an inviting setting for morning coffee, outdoor dining, or entertaining while enjoying the peaceful country surroundings. This property offers an exceptional location with easy access to the villages of Sharon, Millerton, Lakeville, and Salisbury, as well as the Wassaic train station with service to New York City. Nearby amenities include acclaimed private and public schools, scenic hiking trails and conservation areas, the Sharon Playhouse, and year-round recreation at Mohawk Mountain and Catamount Ski Area. A peaceful country setting with convenient access to the best of the Litchfield County and Hudson Valley region.

190 Cornwall Bridge Rd, Sharon

Listing courtesy of Whitney Malagrino from Berkshire Hathaway NE Prop.. (860) 790-9858 (860) 677-7321
25 Bayberry Dr Unit 3, Sharon
$369,900
2 Beds ⋅ 1 Baths ⋅ 73569421 MLS ⋅ ['Sharon Green'] BLDG.
Sunny, Updated & Easy Condo Living! Highly sought-after Sharon Green Condominiums offers this inviting 2-bedroom, 1-bath unit with 913 sq. ft. of comfortable, single-level living. Freshly painted and enhanced with updated lighting, recessed lighting and beautiful new hickory hardwood flooring, this home is move-in ready. The spacious living room features hardwood floors, recessed lighting and access to a private balcony—perfect for morning coffee or unwinding at the end of the day. The fully applianced kitchen offers ample cabinetry, pantry storage and a convenient dining area. A generous foyer welcomes you home. The spacious main bedroom features hickory hardwood flooring, recessed lighting and excellent closet space, while the second bedroom offers matching flooring, chair rail detail and a large closet. Rare low condo fee that includes everything; Heat, Hot Water, Electricity, Gas Cooking, Central A/C, Water, Sewer, Trash Removal, On-site Professional Property Management, Inground Pool, Tennis Courts and Community room. Enjoy the convenient location near shopping, Lake Massapoag, T-Station and major highways.

25 Bayberry Dr Unit 3, Sharon

Listing courtesy of Listing Agent: Debra Parker from Listing Office: RE/MAX Real Estate Center.
120 Sharon Valley Rd, Sharon
$525,000
4 Beds ⋅ 2 Baths ⋅ 24197961 MLS
An exceptional opportunity to own a move-in-ready four-bedroom home just around the corner from the heart of Sharon, offering the Litchfield County lifestyle at a price point increasingly difficult to find. Set on approximately three-quarters of an acre of level land, 120 Sharon Valley Road combines comfortable everyday living with an incredibly convenient location near Sharon's village center, Sharon Hospital, local shops, dining, recreation, and easy access to the New York border. The home is only about 15 minutes from the Metro-North station in Wassaic. Inside, light hardwood floors flow throughout the home, complemented by fresh interior paint and abundant natural light from replacement windows. The flexible four-bedroom layout provides room for family, guests, a home office, or creative space, giving the home functionality well beyond its footprint. The property has been thoughtfully refreshed with a newer driveway, updated landscaping, and a newer deck overlooking the fully fenced backyard-an ideal setting for pets, entertaining, gardening, or simply enjoying the peaceful surroundings. A large backyard shed provides exceptional additional storage for tools, outdoor equipment, bikes, or recreational gear. Downstairs, the walk-out lower level features impressively high ceilings and offers exciting potential for future finished living space, whether envisioned as a family room, home gym, office, workshop, or guest area.

120 Sharon Valley Rd, Sharon

Listing courtesy of AJ Davis from Better Homes and Gardens Real Estate Executive Real Estate. (203) 848-8096 (860) 633-8800
197 N Main St, Sharon
$540,000
2 Beds ⋅ 1 Baths ⋅ 73566706 MLS
Here's your opportunity to buy in Sharon.Our last buyer's financing fell through, so this beautiful home is back and available. That is the buyer's loss and it could be your win. Nothing changed about the home. This was somebody's loan problem, not a problem with the house.197 N Main Street. Two bedrooms, one bath, on a level fenced lot in one of Sharon's most sought after neighborhoods. Brand new high efficiency boiler, passed Title V, a renovated bath, and a granite kitchen you will actually want to cook in. The big ticket items are already handled.We are excited to welcome you and yours home. Come see it this Saturday and bring your offer.Don't miss this rare entry-point to the town of Sharon!

197 N Main St, Sharon

Listing courtesy of Listing Agent: Jimmy Chung Van Duong from Listing Office: Keller Williams Realty.
635 Old Post Road Unit 109, Sharon
$479,900
2 Beds ⋅ 2 Baths ⋅ 73566337 MLS ⋅ ['Woodcrest Run Condominiums'] BLDG.
Welcome to this stunning 2-bedroom, 2-bathroom condo in a sought-after 55+ community in Sharon, MA! This unit features an open floor plan with a spacious living and dining area, large windows, and a private balcony perfect for relaxing. The updated kitchen flows seamlessly, offering plenty of space for entertaining. The master bedroom boasts a private ensuite bath and a walk-in closet. Community amenities include off-street parking, a beautifully maintained common area for gatherings, and an on-site fitness center, 2 exterior parking spots. Conveniently located near Rt 1 with easy access to restaurants, golf courses, and just a short drive to Boston and Providence. This unit is being sold "as-is, where-is." The seller has never occupied the property, allowing you the opportunity to make it your own. Don’t miss out on this incredible opportunity—schedule your showing today! Act fast—this gem won’t last long

635 Old Post Road Unit 109, Sharon

Listing courtesy of Listing Agent: Phillip Gendreau from Listing Office: Strive Realty.
635 Old Post Road Unit 302, Sharon
$489,900
2 Beds ⋅ 2 Baths ⋅ 73566336 MLS ⋅ ['Woodcrest Run Condominiums'] BLDG.
CORNER UNIT! Welcome to this stunning 2-bedroom, 2-bathroom condo in a sought-after 55+ community in Sharon, MA! This unit features an open floor plan with a spacious living and dining area, granite countertops, large windows, and a private balcony perfect for relaxing. The updated kitchen flows seamlessly, offering plenty of space for entertaining. The master bedroom boasts a private ensuite bath and a walk-in closet. Community amenities include off-street parking, a beautifully maintained common area for gatherings, and an on-site fitness center, 2 exterior parking spots. Conveniently located near Rt 1 with easy access to restaurants, golf courses, and just a short drive to Boston and Providence. This unit is being sold "as-is, where-is." The seller has never occupied the property, allowing you the opportunity to make it your own. Don’t miss out on this incredible opportunity—schedule your showing today! Act fast—this gem won’t last long!

635 Old Post Road Unit 302, Sharon

Listing courtesy of Listing Agent: Phillip Gendreau from Listing Office: Strive Realty.
13 Winslow Rd, Sharon
$700,000
3 Beds ⋅ 2 Baths ⋅ 73565315 MLS
This fabulous dormered Cape featuring 2 FULL BATHS and a GARAGE in a DESIRABLE SHARON NEIGHBORHOOD seamlessly blends classic character with incredible LAYOUT FLEXIBILITY. The RENOVATED KITCHEN features GRANITE countertops, STAINLESS steel appliances, a DOUBLE OVEN, and direct access to a DECK overlooking a PRIVATE FENCED BACKYARD with a storage SHED. The kitchen opens smoothly into the LARGE DINING room. The EXPANSIVE front-to-back living room features a cozy FIREPLACE. Originally built as a four-bedroom, the rear portion of the living room can easily be re-converted back into a main-level bedroom per town guidelines—a feature backed by a town-approved 4-bedroom septic system and a FULL MAIN-LEVEL BATH, making it iIDEAL FOR MULTIGENERATIONAL LIVING or a dedicated HOME OFFICE. Upstairs features three comfortable bedrooms, custom built-in drawers, and a SECOND RENOVATED FULL BATH. A fully FINISHED LOWER LEVEL provides flexible space for a home GYM, GAME room, or GUEST area, while the PRIME LOCATION, LOCATION LOCATION puts you moments from Sharon Center, the NEW state-of-the-art high school, NEW public library, Cobb Corner SHOPPING, Costco, and both the Sharon and Canton COMMUTER RAIL stations to Boston and Providence.

13 Winslow Rd, Sharon

Listing courtesy of Listing Agent: Karen Tanzer from Listing Office: Keller Williams Elite - Sharon.
34 Cortland Dr Unit 34, Sharon
$625,000
2 Beds ⋅ 3 Baths ⋅ 73564903 MLS ⋅ ['Macintosh Farms'] BLDG.
SUNDRENCHED best describes this contemporary townhome in highly desired Macintosh Farms...This FABULOUS home showcases GLEAMING HARDWOODS, SOARING ceilings & explodes with NATURAL LIGHT throughout! Enter to views of the DRAMATIC CATHEDRAL living room with GAS FIREPLACE, SKYLIGHTS, OPEN LAYOUT & picture window overlooking the professionally landscaped grounds & opens to the dining room with sliders to a large PRIVATE deck; enjoy the SPACIOUS white OPEN kitchen boasting NATURAL GAS, STAINLESS STEEL appliances & large dining area with picture window allowing the sun in all day long; half bath completes the 1st floor. Retreat upstairs to the SUNFILLED primary suite with CUSTOM walk-in closet & PRIVATE bath with soaking tub, separate shower & double vanity; additional ensuite SPACIOUS bedroom with full bath & laundry. OVERSIZED WALK-OUT LOWER LEVEL offers additional space ready to be finished! SIGNIFICANT UPDATES include ROOF, HVAC and HARDWOODS! Mac Farms community offers clubhouse, pool, tennis, pickleball & more! THIS IS THE ONE YOU'VE BEEN WAITING FOR! PERFECT OPPORTUNITY TO MAKE IT YOUR OWN!!

34 Cortland Dr Unit 34, Sharon

Listing courtesy of Listing Agent: Deborah Piazza from Listing Office: Coldwell Banker Realty - Sharon.
70 Gay St, Sharon
$519,000
4 Beds ⋅ 2 Baths ⋅ 24199566 MLS
Welcome to 70 Gay St! Just minutes from Sharon's town center, this 1947, two-story charmer exudes peaceful and sun-filled vibes! Well sited on a beautiful, large 3.8-acre lot with equal parts wildflowers and lawn, the home is nicely nestled among mature trees, with just the right balance of sun and shade. And if you're an investor or developer, this property affords an excellent subdivision opportunity, with its 3/4-acre minimum zoning. You could consider subdividing the current 3.8 acres into potentially 4 or 5 separate building lots. Interior features: refinished, walnut-stained, oak floors...large living room with wood-burning fireplace...open kitchen/dining with three exposures and updated appliances...repainted interior...excellent closet space...full, dry basement with a Bilco door for easy exterior access...washer/dryer...and new hot water heater in 2023. Exterior features: new roof in 2021...detached, oversized, one-car garage with a connected, covered walkway from the house...large, flat lot with plenty of room to build, add a pool, tennis court, or whatever else your heart desires...and numerous landscaped flowerbeds.

70 Gay St, Sharon

Listing courtesy of Steven Koleno from Beycome of Connecticut. (804) 656-5007 (804) 656-5007
25 Bayberry Dr Unit 4, Sharon
$369,999
2 Beds ⋅ 1 Baths ⋅ 73562762 MLS ⋅ ['Sharon Green'] BLDG.
Welcome to 25 Bayberry Drive, Unit 4, a beautifully updated top-floor condo offering 912 square feet of bright, comfortable living space. This 2-bedroom, 1-bath unit features a kitchen completely renovated in 2024, complete with a gas range, stainless steel appliances, and updated finishes throughout. The sun-filled living room is highlighted by large windows and new sliding glass doors that open to a private balcony, creating a natural extension of the living space. Both bedrooms feature oversized closets, while the bathroom has been refreshed with updated flooring and a newer vanity. Additional conveniences include common laundry within the building, plus heat, hot water and central air included in the association fee. Residents of Sharon Green also enjoy access to the community pool. Conveniently located near shopping, dining, major routes, and transportation options, Unit 4 offers an updated interior, generous storage, and private outdoor space in one inviting package.

25 Bayberry Dr Unit 4, Sharon

Listing courtesy of Listing Agent: Scanlon Sells Team from Listing Office: eXp Realty LLC - Corporate Office.
99 King Hill Rd, Sharon
$585,000
2 Beds ⋅ 1 Baths ⋅ 24197956 MLS
Circa 1800s Colonial nestled on a picturesque two-acre parcel along a bucolic country road in Sharon, Connecticut, one of Litchfield County's most sought-after towns. Set back on a gentle rise, the property enjoys a peaceful setting with a backyard framed by mature trees. Rich in history and architectural character, this charming two-bedroom cottage showcases timeless craftsmanship and enduring New England appeal. The light-filled interior features a spacious great room with a wood-burning fireplace and a bay-windowed dining area ideal for gathering. A thoughtfully renovated country kitchen features butcher block countertops, a farmhouse sink with brass bridge faucet, and stainless-steel appliances. Recent improvements include freshly painted interiors and exterior, along with a new gravel driveway. A detached barn offers exceptional versatility as a studio, workshop, potting shed, or creative retreat-particularly appealing to the gardening enthusiast. This inviting country home offers a rare opportunity to enjoy the beauty, charm, and quintessential lifestyle of Litchfield County.

99 King Hill Rd, Sharon

Listing courtesy of Julie Einhorn from Compass Connecticut, LLC. (347) 853-1426 (203) 293-9715
142 S Main St, Sharon
$649,900
3 Beds ⋅ 2 Baths ⋅ 73556859 MLS
Located in the heart of Sharon this wonderfully maintained and deleading compliant home offers the perfect blend of charm, warmth, and convenience. A window-lined foyer welcomes you and leads into a spacious living room where a classic bay window creates an inviting space for family and friends to gather. The open floor plan flows through an archway into the dining area and the well-appointed and updated kitchen with a pantry nook and connection to a separate storage area. The primary suite, located in the back of the house for maximum privacy and tranquility, features a walk-in closet and a full renovated bath. Two additional queen-size bedrooms with plentiful closets and a second full bathroom complete the single-level living space. Gas heating and AC assure comfort year round. Exterior features a one-car garage with an extra wide driveway, a large stone patio, and a level backyard. Roof, septic, heating system, AC condenser, vinyl siding, windows, kitchen, bathrooms, full deleading compliance, and other improvements have all been completed since 2015 - all the hard work is already done! Walking distance to the center of town, commuter rail, multiple houses of worship, Lake Massapoag, the new High School, and Ames Street playground. This home is a must see!

142 S Main St, Sharon

Listing courtesy of Listing Agent: Abigail Phillips from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
39 Hospital Hill Rd, Sharon
$495,000
4 Beds ⋅ 4 Baths ⋅ 24194672 MLS
Exceptional Turnkey Investment Opportunity in Sharon, CT! Currently generating $3,700/month in immediate, documented income with active tenancies in place, this well-maintained side-by-side duplex is a rare, high-yielding Litchfield County asset. Each side features a nice 2-bedroom, 1.5-bathroom layout highlighting updated kitchens featuring stainless steel appliances, tile backsplashes, rich hardwood floors, and updated bath fixtures. Both units offer bright, inviting living spaces, dedicated basement laundry with included washers and dryers, and separate mechanicals. Tenants enjoy delightful outdoor living space, including shared, expansive covered front and rear porches. Unbeatable in-town location-situated just moments from the historic Sharon Town Green, local shops, cafes, Sharon Hospital, the Hotchkiss Library, and a short drive to The Hotchkiss School and Lakeville Lake. A seamless, low-maintenance addition to any investment portfolio offering proven cash flow and instant yield from day one!

39 Hospital Hill Rd, Sharon

Listing courtesy of Tanner Sneed from Elyse Harney Real Estate. (860) 671-3241 (860) 435-0120
190 N. Main Street, Sharon
$665,000
3 Beds ⋅ 2 Baths ⋅ 73555384 MLS
Opportunity awaits in this classic Sharon home filled with character, charm, and endless potential. Offering 1,761 sq ft of living space on a sprawling 54,450 sq ft lot, this 3 bedroom, 2 bath property features a formal living room with fireplace, formal dining room, and a fully finished third floor bonus room perfect for a home office, playroom, or additional living space. An updated porch provides the perfect place to relax and enjoy the scenic backyard with views of Sawmill Pond and surrounding nature. Major updates include a furnace and electrical system completed in 2024. While the home does require TLC and updating, it offers great bones, timeless character, and an exceptional opportunity to build equity in a desirable Sharon location. Conveniently located near major commuter routes, the Sharon MBTA Commuter Rail station, schools, shopping, restaurants, and local amenities. A rare chance to restore and personalize a home with outstanding potential.

190 N. Main Street, Sharon

Listing courtesy of Listing Agent: Cheryl Walsh from Listing Office: C. Walsh Realty, Inc..
88 Sharon Valley Rd, Sharon
$699,000
4 Beds ⋅ 2 Baths ⋅ 24193519 MLS
1900 Farm House Homestead on 6.9 Picture-Perfect Acres Enjoy 6.9 sprawling, gently sloping, sunlit acres of cleared meadows, mature landscaping, and Indian Lake Creek framing the back boundary line of the property. This gentleman's farm is fully set up for equine enthusiasts and homesteading. The impressive multi-use barn features two horse stalls, a chicken coop w/eight coops, hayloft, ample space for tractor, storage, & equipment. Barn is outfitted w/electricity & water & there is a run-in on each cleared meadow, plus 2 sheds. Back entrance to a large mud room/pantry area with washer/dryer leads to an open LR/DR/kitchen area combining rustic charm with beams, vaulted ceiling, new appliances, ceiling fans & an abundance of natural sunlight complimented by sky lights. An additional Family Room/Office w/hard wood floors and a Full Bath on main level. Upstairs are 4 Bedrooms & a 2nd Full Bath. A heated storage room separates the house from a 2 car attached, heated garage that includes a brand new, never used generator. Numerous cultural & recreational activities for every season - Sharon Playhouse, Lime Rock Park Racetrack, Mudge Pond, Hiking Trails, Ski Slopes & prestigious Private Schools. Open, enchanting vistas & many more amenities to experience in the precious NW corner of CT. 15 minutes to Metro North. Bring your horses, goats, & chickens & start a homestead, or simply enjoy the peace & beauty of the wide-open acreage. This turn-of-the century gem is ready for you

88 Sharon Valley Rd, Sharon

Listing courtesy of Karen Grimaldi from William Pitt Sotheby's Int'l. (860) 480-1156 (860) 435-2400
635 Old Post Road - Woodcrest Run Unit 2-211, Sharon
$525,000
2 Beds ⋅ 2 Baths ⋅ 73555074 MLS ⋅ ['Woodcrest Run'] BLDG.
Woodcrest Run is a LUXURY 55+ 7 year old community with DEEDED UNDERGROUND PARKING and Elevator. ALL APPLIANCES INCLUDED. FABULOUS Sun filled CORNER UNIT WITH 1187 SQ FT AND 2 BRS 2 BATHS offers Elegant Features Throughout. HARDWOOD, Quartz Countertops in KItchen and Baths, White Cabinets, SS appliances and subway tile backsplash in Kitchen and Tiled bathrooms and Showers are just a few of the high-end features. 9 FT CEILINGS & beautiful CROWN MOLDING in the OPEN CONCEPT Living Room, Dining Room and Kitchen. Generous closets, including custom 13' WALK-IN CLOSET IN PRIMARY BEDROOM. THE OVERSIZED WINDOWS SUPPLEMENT THE GORGEOUS VIEWS AND LET THE SUN STREAM IN. Situated in quiet location with Picturesque Views from the 8x4 PRIVATE BALCONY minutes from Patriot Place, Brigham and Women's Health Center, Rt.1 & Rt.95 plus easy access to 3 commuter rail stations UNDERNEATH GARAGE SPOT INCLUDED + Outside Deeded Sot. Storage unit included. Woodcrest AMENITIES include an ELEVATOR, COMMUNITY ROOM w/ KITCHEN and FITNESS AREA. also SOLARIUM on 3rd floor.Welcome to Woodcrest Run, a 55+ Luxury Community. Abutting gorgeous Walpole Country Club, this special 2 bedroom, 2 bathroom END UNIT offers elegant finishes throughout. Abundant oversized windows, deep toned flooring and attractive quartz countertops in kitchen and baths, white cabinetry, upgraded SS appliances and subway tile backsplash in kitchen and neutral colored tiled baths and shower surrounds. 9' ceilings and rich crown molding in the open concept floorplan. Generous closets, including custom 13' deep walk-in. DEEDED GARAGE PARKING SPACE plus assigned outside parking , and guest parking 6x5 Storage unit also included. Situated in quiet end location with picturesque views from the 8x4 private balcony, minutes from Patriot Place, Brigham and Women's, Rt.1 & Rt.95 plus easy access to 3 commuter rail stations. Amenities include an elevator, community room with kitchen area, fitness room and solarium on 3rd floor.

635 Old Post Road - Woodcrest Run Unit 2-211, Sharon

Listing courtesy of Listing Agent: Roni Thaler from Listing Office: Coldwell Banker Realty - Sharon.
94 Jackson Rd, Sharon
$499,500
2 Beds ⋅ 1 Baths ⋅ 24192359 MLS
SEASONAL VIEWS! Perched along a quiet country road and completely surrounded by the beauty of nature, this beautifully updated 2-bedroom, 1-bathroom home offers the perfect blend of modern luxury and peaceful rural living. Whether you are looking for a full-time sanctuary or a weekend getaway, this property delivers wide-open spaces and total serenity-all just minutes from town. The heart of the home features premium stainless steel appliances, sleek countertops, custom cabinetry, and a thoughtful layout designed for effortless entertaining and cooking. Step into a bright, airy living space framed by views of the surrounding landscape. The home boasts an inviting flow, highlighted by the stunning new kitchen that opens up to the main living areas. Both bedrooms offer cozy, peaceful retreats at the end of the day, accompanied by a well-appointed full bathroom. The detached 2-Car Garage with loft to Keep your vehicles protected from the elements, and utilize the expansive loft space above as a home office, artist studio, gym, or extra storage. Step outside onto your brand new, private deck. It's the ultimate spot for morning coffee, evening stargazing, or hosting summer barbecues against a backdrop of mature trees and wildlife. Outside, the acreage provides plenty of room to garden, play, or simply soak in the unobstructed views of the great outdoors. Schedule your private tour today and experience country living at its absolute finest.

94 Jackson Rd, Sharon

Listing courtesy of Roxanne Belter from William Pitt Sotheby's Int'l. (860) 318-1583 (860) 435-2400
31 Bayberry Dr Unit 4, Sharon
$299,500
1 Beds ⋅ 1 Baths ⋅ 73546128 MLS ⋅ ['Sharon Green'] BLDG.
Presenting an exceptional opportunity at 31 Bayberry Dr U:4, Sharon, MA, this 1972 condominium offers a meticulously designed living space spanning 737 square feet. This top-floor residence provides a distinctive blend of comfort and accessibility, ideally suited for refined urban living. The condominium features a thoughtfully arranged single bedroom, providing a private and serene retreat. Complementing this, a full bathroom is appointed with contemporary fixtures, ensuring convenience and sophisticated functionality. This one-story property is strategically located, offering an effortless flow throughout the living areas. Discover the potential for an elevated lifestyle by inquiring about this distinguished condominium.

31 Bayberry Dr Unit 4, Sharon

Listing courtesy of Listing Agent: Leslie Zhang from Listing Office: Coldwell Banker Realty - Sharon.
314 Mountain Rd, Sharon
$525,000
5 Beds ⋅ 2 Baths ⋅ 5098374 MLS
Looking to unplug and get away from it all? Here's your chance! There aren't many opportunities like this one left - close enough to Boston but in the middle of no where, these two seasonal cottages on 14.8 acres offer walking trails that allow access to the Wapack trail and there is a lovely pond that has been swimmable in the past - "water so clear you could see a quarter on the bottom". Surrounded by land owned by the New England Forestry Foundation, this could make for a perfect summer vacation compound - two separate buildings, the stone house with one bedroom, a bath, a loft, a floor to ceiling stone fireplace, a woodstove in the kitchen and a newer roof. The ranch has one bath and four bedrooms, two of which have separate access and can be locked, as well as a large screened porch that looks down over the pond. It also has a full basement with an old oil burning furnace (it is not currently operational), but all the duct work is in place and accessible. There is also a one car detached garage by the road. While they are rustic and will require work, they are equipped with updated electricity, phone lines, and running water, and there is even a security system. Located at the end of a seasonal road (which could potentially be accessed in the winter by snowmobile), this is a rare chance to escape and create a peaceful, idyllic retreat, or perhaps an Airbnb opportunity? If the idea of total peace and quiet that is not too far off the beaten path is what you seek, then roll up your sleeves and make it happen! Sharon is a lovely small town in the best kept secret in NH - The Monadnock Region - with easy access to the Massachusetts border and only an hour and half to Boston.

314 Mountain Rd, Sharon

Listing courtesy of Matthew W Cabana from EXP Realty. (Cell: 603-933-2991)
71 Hospital Hill Rd, Sharon
$675,000
2 Beds ⋅ 1 Baths ⋅ 24187245 MLS
This c. 1880 Colonial is nestled in the heart of the Village of Sharon. Thoughtfully restored from top to bottom, it is a truly turnkey offering that seamlessly blends Founding Era character with modern comfort. Inside, warm, inviting living spaces are filled with natural light and include a well-appointed kitchen with breakfast nook, two bedrooms, one beautifully finished bath, a living room and formal dining room. There is an additional room downstairs plus a dedicated laundry room. Every detail of the renovation was carefully executed to preserve the home's historic charm while introducing the quality, efficiency, and craftsmanship expected in a modern residence. Recent improvements include a new roof with custom gutters, new mechanical systems, fully restored windows, and a complete professional repaint. Designed to embrace its exceptional setting, the rear porch captures sweeping southern views across the surrounding landscape. Professionally landscaped grounds feature orchards, formal parterres, and mature gardens that provide year-round beauty and a peaceful sense of retreat. Rarely does a historic home offer such a complete restoration in one of Sharon's most desirable locations. With timeless architecture, beautifully curated gardens, and exceptional outdoor living framed by expansive southern views, this is a home of enduring beauty and effortless livability.

71 Hospital Hill Rd, Sharon

Listing courtesy of Dan Kessler from Compass Connecticut, LLC. (917) 455-5191 (203) 293-9715
32 Bayberry Dr Unit 3, Sharon
$388,000
2 Beds ⋅ 1 Baths ⋅ 73543543 MLS ⋅ ['Sharon Green'] BLDG.
The best of country living located as little as 30 minutes away from major cities in the vicinity. Imagine a world with no more utility bills as the condo fee covers everything. This is a wonderful opportunity to live in this community with a great school system where the bus picks up and drops off right in the front yard.

32 Bayberry Dr Unit 3, Sharon

Listing courtesy of Listing Agent: Kris Lippi from Listing Office: Get Listed Realty, LLC.
24 Pleasant Park Rd, Sharon
$620,000
3 Beds ⋅ 1 Baths ⋅ 73541714 MLS
BEST VALUE ~YOUR SEARCH IS OVER! Simply SUNDRENCHED & INVITING, this BEAUTIFULLY maintained 3-bedroom, 1 bath home is tucked at the end of a cul-de-sac on a generous, PRIVATE lot... just moments from everything Sharon has to offer! Boasting approx 1500 sq ft of FABULOUS living space, NATURAL LIGHT pours through every room, highlighting GLEAMING HARDWOOD FLOORS & TIMELESS CHARM. The FIREPLACED living room offers a warm, welcoming space for relaxing or entertaining, while the STUNNING sunroom is lined w/WALLS OF WINDOWS & creates a BRIGHT, AIRY retreat perfect for morning coffee w/FRENCH DOORS leading to the LARGE deck overlooking PEACEFUL wooded grounds beyond. Three comfortable bedrooms provide flexibility for today’s lifestyle. The kitchen is SPACIOUS w/plenty of cabinetry, functional layout & VENTED HOOD. NATURAL GAS, CENTRAL AIR & 1 CAR GARAGE. Ideally located near top-rated schools, commuter rail, shops, and dining... THIS HOME BLENDS TRANQUILITY WITH EVERYDAY CONVENIENCE!

24 Pleasant Park Rd, Sharon

Listing courtesy of Listing Agent: Deborah Piazza from Listing Office: Coldwell Banker Realty - Sharon.
142 Gay St, Sharon
$575,000
3 Beds ⋅ 1 Baths ⋅ 24183989 MLS
Step inside the newly reborn 142 Gay Street. This village home, held by the same loving family for decades, has undergone a head-to-toe transformation. Forget the hassle of renovations. We're talking new plumbing, new wiring, fresh paint, refinished floors, and sleek new appliances throughout. But while the renovations are cutting-edge, the charm remains. You'll love the cozy layout, complete with an eat-in kitchen, a spacious living room centered around a classic wood-burning fireplace, and a versatile sunroom perfect for your home office or den. The 1.28-acre lot is a wide-open, level canvas just waiting for your landscaping vision (and maybe that pool you've always wanted!). With an unbeatable location steps away from the Sharon Farm Market, town lake, and local favorites like J. P. Giffords and Le Gamin restaurant, this is the fresh start you've been looking for. Don't wait-come see this Litchfield County treasure today!

142 Gay St, Sharon

Listing courtesy of Amy Longley from William Pitt Sotheby's Int'l. (860) 671-9400 (860) 435-2400

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