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Tucked away at the end of a long private driveway, this 3,794-square-foot custom home offers four bedrooms on nine scenic acres, with potential for a free land split. Wood flooring milled from trees on the property, natural beams and built-ins lend warmth and character. Every door is custom made; the doors, staircase treads and living room floor are Brazilian cherry. A pass-through stone-and-brick fireplace anchors the living space, while steel-beam construction extends through the house, basement and garage. The granite kitchen features an island, new hardware and a new commercial-grade propane range with 10 burners and double ovens. Windows surround the four-season great room, bringing in light and views year-round. A first-floor primary suite offers one-floor living. Above the oversized two-car garage, a cathedral-ceiling bonus room offers flexible space for an office, studio or guests. Updates include an automatic Generac generator, 2009 roof, new garage doors, stainless-steel chimney liner, repointed chimney, new gutters, gas lines, tamper-resistant outlets, lighting, new dishwasher, a new boiler (February 2026) and fresh paint. Enjoy privacy close to schools, restaurants, shopping and I-395 in Woodstock.

4 Beds ⋅ 2 Baths ⋅ 24206040 MLS

Tucked away at the end of a long private driveway, this 3,794-square-foot custom home offers four bedrooms on nine scenic acres, with potential for a free land split. Wood flooring milled from trees on the property, natural beams and built-ins lend warmth and character. Every door is custom made; the doors, staircase treads and living room floor are Brazilian cherry. A pass-through stone-and-brick fireplace anchors the living space, while steel-beam construction extends through the house, basement and garage. The granite kitchen features an island, new hardware and a new commercial-grade propane range with 10 burners and double ovens. Windows surround the four-season great room, bringing in light and views year-round. A first-floor primary suite offers one-floor living. Above the oversized two-car garage, a cathedral-ceiling bonus room offers flexible space for an office, studio or guests. Updates include an automatic Generac generator, 2009 roof, new garage doors, stainless-steel chimney liner, repointed chimney, new gutters, gas lines, tamper-resistant outlets, lighting, new dishwasher, a new boiler (February 2026) and fresh paint. Enjoy privacy close to schools, restaurants, shopping and I-395 in Woodstock.

555 Senexet Rd, Woodstock

$650,000

This 4-bedroom, 2591sqft Cape is on cul-de-sac, conveniently located in South Woodstock. Offering combination of classic character with hardwood floors and comfortable living spaces, this single owner home is ready for it's next chapter. The main level living area is all hardwoods, with a kitchen/dining combination, a living room with a propane fireplace, and an office with tons of built-ins. Come in from the garage that is equipped with shelving and a set tub, to the mudroom with open locker style storage. Privately tucked to the rear of the main floor is the primary suite, with a large walk in closet, and full bath. The 2nd level is a surprise with 3 good sized bedrooms, a full bath, a great closet storage space, and a future living space, already studded with rough plumbing and electric. The level back yard offers room to relax, play, garden, or entertain. The irrigation system will keep the lawn green. No HOA, Senexet Village Road is town owned, and also hosts a recreation area for all to use.

4 Beds ⋅ 3 Baths ⋅ 24197102 MLS

This 4-bedroom, 2591sqft Cape is on cul-de-sac, conveniently located in South Woodstock. Offering combination of classic character with hardwood floors and comfortable living spaces, this single owner home is ready for it's next chapter. The main level living area is all hardwoods, with a kitchen/dining combination, a living room with a propane fireplace, and an office with tons of built-ins. Come in from the garage that is equipped with shelving and a set tub, to the mudroom with open locker style storage. Privately tucked to the rear of the main floor is the primary suite, with a large walk in closet, and full bath. The 2nd level is a surprise with 3 good sized bedrooms, a full bath, a great closet storage space, and a future living space, already studded with rough plumbing and electric. The level back yard offers room to relax, play, garden, or entertain. The irrigation system will keep the lawn green. No HOA, Senexet Village Road is town owned, and also hosts a recreation area for all to use.

23 Senexet Village Rd, Woodstock

$599,000

Perfect Countryside Elegance. Welcome to 511 Perrin Road, an exceptional country estate gracefully set atop a private 3.5-acre hillside in scenic Woodstock. A long paved driveway winds through picturesque grounds to this beautifully crafted home, where timeless architecture meets modern efficiency with 100% owned solar. Designed for effortless one-floor living, the residence features a luxurious first-floor primary suite, private executive office, gleaming hardwood floors, exquisite custom built-ins, and an inviting open living and dining area anchored by a dramatic back to back wood-burning fireplace. The custom Brunarhans kitchen is a showcase of quality craftsmanship and thoughtful design. The home boasts 2,393 SqFt of finished living space with 2.5 baths. The second level offers a spacious guest bedroom, full bath, and a connected bonus room, providing exceptional flexibility for family and guests. Step outside to enjoy the serenity of the private patio, a charming pond, and sweeping open grounds. The expansive lawn offers outstanding potential for a boutique vineyard, gardens, or equestrian pursuits, with horses and household pets permitted and ample room for paddocks. Completing this remarkable property is an oversized two-car garage with a private workshop. A rare combination of privacy, elegance, sustainability, and refined country living. A truly exceptional offering in one of Woodstock's most desirable locations.

2 Beds ⋅ 3 Baths ⋅ 24187780 MLS

Perfect Countryside Elegance. Welcome to 511 Perrin Road, an exceptional country estate gracefully set atop a private 3.5-acre hillside in scenic Woodstock. A long paved driveway winds through picturesque grounds to this beautifully crafted home, where timeless architecture meets modern efficiency with 100% owned solar. Designed for effortless one-floor living, the residence features a luxurious first-floor primary suite, private executive office, gleaming hardwood floors, exquisite custom built-ins, and an inviting open living and dining area anchored by a dramatic back to back wood-burning fireplace. The custom Brunarhans kitchen is a showcase of quality craftsmanship and thoughtful design. The home boasts 2,393 SqFt of finished living space with 2.5 baths. The second level offers a spacious guest bedroom, full bath, and a connected bonus room, providing exceptional flexibility for family and guests. Step outside to enjoy the serenity of the private patio, a charming pond, and sweeping open grounds. The expansive lawn offers outstanding potential for a boutique vineyard, gardens, or equestrian pursuits, with horses and household pets permitted and ample room for paddocks. Completing this remarkable property is an oversized two-car garage with a private workshop. A rare combination of privacy, elegance, sustainability, and refined country living. A truly exceptional offering in one of Woodstock's most desirable locations.

511 Perrin Rd, Woodstock

$520,000

Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases its original door with full exterior shutters, a hallmark of Greek Revival style. The living room centers on a classic fireplace, and along the upstairs landing a wall of built-in bookshelves creates a welcoming library space. Three bedrooms are located on the second floor, with an additional first-floor room currently serving as a fourth bedroom. The primary includes a walk-in closet and bath with a clawfoot tub. The walk-up attic offers potential for an office, playroom, or studio. The kitchen features a custom layout paired with quality appliances (Sub-Zero fridge & Thor cooktop) and the warmth of a wood stove. Updates include new Trex decking and a newly finished three-season room off the dining room. Historic touches, such as unique wallcoverings and original details, remain intact, blending history, artistry, and the timeless charm of living in Woodstock, CT. Property to be sold in as-is condition.

4 Beds ⋅ 3 Baths ⋅ 24125003 MLS

Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases its original door with full exterior shutters, a hallmark of Greek Revival style. The living room centers on a classic fireplace, and along the upstairs landing a wall of built-in bookshelves creates a welcoming library space. Three bedrooms are located on the second floor, with an additional first-floor room currently serving as a fourth bedroom. The primary includes a walk-in closet and bath with a clawfoot tub. The walk-up attic offers potential for an office, playroom, or studio. The kitchen features a custom layout paired with quality appliances (Sub-Zero fridge & Thor cooktop) and the warmth of a wood stove. Updates include new Trex decking and a newly finished three-season room off the dining room. Historic touches, such as unique wallcoverings and original details, remain intact, blending history, artistry, and the timeless charm of living in Woodstock, CT. Property to be sold in as-is condition.

101 Child Hill Rd, Woodstock

$509,000

Looking for a home that exudes the character and craftsmanship of bygone days without the challenges of a true antique? 15 Paine District Road looks and feels like it's been here for centuries, but this gorgeous reproduction Saltbox is less than 40 years old. Hand-built by its original owner with extraordinary attention to craftsmanship and period-inspired detail, it offers the warmth and character of early New England architecture recreated for modern living. Huge blocks of granite form the entry steps to each of the three doors, while exposed rough hewn beams and an oversized fireplace harken back to quieter days. Custom cabinetry and millwork by the renowned craftsmen at Brunarhans can be found throughout the home, from the solid wood kitchen, custom chair rails and molding to the raised paneled wall surrounding the fireplace. The kitchen features a cooking island and charming bay window dining nook with built-in seating. The flexible floor plan offers 3 bedrooms, including one on the first floor currently used as an office with more beautiful built in floor to ceiling custom cabinetry. The second floor offers a spacious primary and two additional bedrooms, the smaller one currently being used as a separate laundry area and playroom. The spacious garage includes a workshop area and storage loft. If you think this property looks pretty now, just imagine it with the bloom of foliage. Act now and you can be moved in by peak leaf season, your pumpkins and scarecrow await!

3 Beds ⋅ 2 Baths ⋅ 24204065 MLS

Looking for a home that exudes the character and craftsmanship of bygone days without the challenges of a true antique? 15 Paine District Road looks and feels like it's been here for centuries, but this gorgeous reproduction Saltbox is less than 40 years old. Hand-built by its original owner with extraordinary attention to craftsmanship and period-inspired detail, it offers the warmth and character of early New England architecture recreated for modern living. Huge blocks of granite form the entry steps to each of the three doors, while exposed rough hewn beams and an oversized fireplace harken back to quieter days. Custom cabinetry and millwork by the renowned craftsmen at Brunarhans can be found throughout the home, from the solid wood kitchen, custom chair rails and molding to the raised paneled wall surrounding the fireplace. The kitchen features a cooking island and charming bay window dining nook with built-in seating. The flexible floor plan offers 3 bedrooms, including one on the first floor currently used as an office with more beautiful built in floor to ceiling custom cabinetry. The second floor offers a spacious primary and two additional bedrooms, the smaller one currently being used as a separate laundry area and playroom. The spacious garage includes a workshop area and storage loft. If you think this property looks pretty now, just imagine it with the bloom of foliage. Act now and you can be moved in by peak leaf season, your pumpkins and scarecrow await!

15 Paine District Rd, Woodstock

$489,900

TO BE BUILT Welcome to the quiet corner of Northeast Connecticut. Serene setting in Woodstock, this Raised Ranch on 2 +/- acres will provide ample living space with 1500sq ft. on the main floor. A two car garage underneath and unfinished basement space allows room for expansion. 3 bedrooms, two baths. Central heat and air, granite or similar counter tops. Generator hook up. Cathedral ceilings through living room and kitchen. Farmhouse style interior doors. Vinyl plank flooring. Paint colors, lighting, and cabinet style to be determined. Walk out basement and 12 x 12 pressure treated deck off kitchen for summer barbecue or relaxing on those warm summer nights.

3 Beds ⋅ 2 Baths ⋅ 24146059 MLS

TO BE BUILT Welcome to the quiet corner of Northeast Connecticut. Serene setting in Woodstock, this Raised Ranch on 2 +/- acres will provide ample living space with 1500sq ft. on the main floor. A two car garage underneath and unfinished basement space allows room for expansion. 3 bedrooms, two baths. Central heat and air, granite or similar counter tops. Generator hook up. Cathedral ceilings through living room and kitchen. Farmhouse style interior doors. Vinyl plank flooring. Paint colors, lighting, and cabinet style to be determined. Walk out basement and 12 x 12 pressure treated deck off kitchen for summer barbecue or relaxing on those warm summer nights.

00 Center Rd, Woodstock

$374,900

Really does a two-family home ever come on the market in Woodstock, never mind one on 3.5 acres. Even more rare is finding a two-family home you can live in with a large commercial/industrial garage for all of your toys, projects, and potential business use. Property consists of two, 2 bedroom-1-bathroom apartments. Each unit paying their own electric/heat. The lower garage has its own electric panel, heat and even a half bathroom. Oversized 10-foot brand new garage door along with steel I-beam construction. Proper property has a newer septic system, and a modern drilled well.

4 Beds ⋅ 2 Baths ⋅ 24209768 MLS

Really does a two-family home ever come on the market in Woodstock, never mind one on 3.5 acres. Even more rare is finding a two-family home you can live in with a large commercial/industrial garage for all of your toys, projects, and potential business use. Property consists of two, 2 bedroom-1-bathroom apartments. Each unit paying their own electric/heat. The lower garage has its own electric panel, heat and even a half bathroom. Oversized 10-foot brand new garage door along with steel I-beam construction. Proper property has a newer septic system, and a modern drilled well.

616 Rte 197, Woodstock

$369,000

Welcome to easy one-floor living at 1310 Route 169 in desirable Woodstock! Set on 0.6 acre, this thoughtfully updated home offers comfort, convenience and a peaceful outdoor setting. Step onto the large deck and enjoy a beautiful open backyard, where gardens and woodland views create a private retreat for morning coffee, summer gatherings or simply unwinding. Inside, updated flooring and granite countertops in the kitchen and bathroom add style, while the dining room window welcomes natural light. First-floor laundry makes everyday living easier. The open walk-out basement offers room for hobbies, storage and potential future expansion, with a pellet stove for added warmth. Numerous improvements include updated doors, a new water heater in 2023, and a freshly updated bathroom vanity. A new 20x20 two-car carport, added in 2026, complements the asphalt driveway. The 1,500-gallon septic tank was replaced in 2021 and the roof in 2011. A washer, dryer and generator with a whole-house plug-in connection are included. Enjoy the charm of Northeast Connecticut with convenient access to Massachusetts and I-395 in Putnam - a welcoming place to settle in and make your own.

3 Beds ⋅ 1 Baths ⋅ 24210680 MLS

Welcome to easy one-floor living at 1310 Route 169 in desirable Woodstock! Set on 0.6 acre, this thoughtfully updated home offers comfort, convenience and a peaceful outdoor setting. Step onto the large deck and enjoy a beautiful open backyard, where gardens and woodland views create a private retreat for morning coffee, summer gatherings or simply unwinding. Inside, updated flooring and granite countertops in the kitchen and bathroom add style, while the dining room window welcomes natural light. First-floor laundry makes everyday living easier. The open walk-out basement offers room for hobbies, storage and potential future expansion, with a pellet stove for added warmth. Numerous improvements include updated doors, a new water heater in 2023, and a freshly updated bathroom vanity. A new 20x20 two-car carport, added in 2026, complements the asphalt driveway. The 1,500-gallon septic tank was replaced in 2021 and the roof in 2011. A washer, dryer and generator with a whole-house plug-in connection are included. Enjoy the charm of Northeast Connecticut with convenient access to Massachusetts and I-395 in Putnam - a welcoming place to settle in and make your own.

1310 Rte 169, Woodstock

$285,000

This 3-bedroom Cape Cod has a ton of potential! Located in a peaceful lake neighborhood, and within walking distance of a beach, this property offers plenty of opportunity to get outside and enjoy the outdoors. If you need a break from the water, enjoy the large private back deck that's perfect for relaxing, hosting, and more. The plumbing system did not hold pressure at time of winterization, indicating possible plumbing damages are present and water will not be on for inspections. If property was built prior to 1978, Lead Based Paint Potentially Exists. Highest & Best Hold Period active - expires 08/19/2026 01:00 PM CST

3 Beds ⋅ 2 Baths ⋅ 24198608 MLS

This 3-bedroom Cape Cod has a ton of potential! Located in a peaceful lake neighborhood, and within walking distance of a beach, this property offers plenty of opportunity to get outside and enjoy the outdoors. If you need a break from the water, enjoy the large private back deck that's perfect for relaxing, hosting, and more. The plumbing system did not hold pressure at time of winterization, indicating possible plumbing damages are present and water will not be on for inspections. If property was built prior to 1978, Lead Based Paint Potentially Exists. Highest & Best Hold Period active - expires 08/19/2026 01:00 PM CST

40 Crooked Trl, Woodstock

$175,000

Welcome to 4 Fawn Ridge in Woodstock! This inviting condo offers a wonderful opportunity to enjoy the ease and convenience of condo living in a peaceful setting. Featuring a functional layout with comfortable living spaces, this home provides a great foundation for its next owner. Offering a great opportunity to add your own personal touches, this condo has solid potential and is ready for its next owner to make it their own. Bring your ideas and vision to create a space that truly reflects your style. Enjoy the charm of Woodstock while remaining conveniently located near local amenities, shopping, dining, recreation, and major routes. Whether you're looking for your first home, downsizing, or simply searching for a low-maintenance lifestyle, this property is worth a look. Schedule your private showing today and come see the possibilities at 4 Fawn Ridge Rd! (Photos virtually enhanced and staged)

2 Beds ⋅ 1 Baths ⋅ 24205739 MLS ⋅ Fawn Ridge BLDG.

Welcome to 4 Fawn Ridge in Woodstock! This inviting condo offers a wonderful opportunity to enjoy the ease and convenience of condo living in a peaceful setting. Featuring a functional layout with comfortable living spaces, this home provides a great foundation for its next owner. Offering a great opportunity to add your own personal touches, this condo has solid potential and is ready for its next owner to make it their own. Bring your ideas and vision to create a space that truly reflects your style. Enjoy the charm of Woodstock while remaining conveniently located near local amenities, shopping, dining, recreation, and major routes. Whether you're looking for your first home, downsizing, or simply searching for a low-maintenance lifestyle, this property is worth a look. Schedule your private showing today and come see the possibilities at 4 Fawn Ridge Rd! (Photos virtually enhanced and staged)

4 Fawn Rdg Unit 4, Woodstock

$74,900

Imagine waking each morning to shimmering lake views and the peaceful sounds of nature. Tucked away on a quiet dead-end road in Woodstock's coveted Quassett Lake community, this exceptional homesite offers the rare opportunity to create a custom retreat in one of northeastern Connecticut's most treasured settings. Perched above the road with a gentle rise in elevation, the property enjoys beautiful direct views of Quassett Lake, with the potential to enhance those vistas through selective tree clearing. Just a short stroll away, the neighborhood lake access invites you to spend your days swimming, kayaking, boating, fishing, or simply soaking in the tranquility of lakeside living. A 2016 perc test and A-2 survey are also available, offering additional confidence as you begin planning your dream home. Whether you envision a timeless architectural masterpiece, a modern lakeside escape, or a peaceful year-round residence, this is a place where your vision can truly come to life. Opportunities to build with lake views in Quassett Lake are exceptionally rare- don't miss your chance to create something extraordinary!

24186921 MLS

Imagine waking each morning to shimmering lake views and the peaceful sounds of nature. Tucked away on a quiet dead-end road in Woodstock's coveted Quassett Lake community, this exceptional homesite offers the rare opportunity to create a custom retreat in one of northeastern Connecticut's most treasured settings. Perched above the road with a gentle rise in elevation, the property enjoys beautiful direct views of Quassett Lake, with the potential to enhance those vistas through selective tree clearing. Just a short stroll away, the neighborhood lake access invites you to spend your days swimming, kayaking, boating, fishing, or simply soaking in the tranquility of lakeside living. A 2016 perc test and A-2 survey are also available, offering additional confidence as you begin planning your dream home. Whether you envision a timeless architectural masterpiece, a modern lakeside escape, or a peaceful year-round residence, this is a place where your vision can truly come to life. Opportunities to build with lake views in Quassett Lake are exceptionally rare- don't miss your chance to create something extraordinary!

182 Baxter Rd, Woodstock

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