The Matthews GroupWilliam Raveis

The Matthews Group

Highland Lake Real Estate

Highland Lake Homes for SaleFind current listings for Highland Lake real estate below. You may also be interested in viewing available Litchfield County lakefront homes.

Browse Highland Lake CT Homes for Sale

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132 Spencer Hill Road Winchester CT 06098

MLS Number 170207910

  • Land
  • Acreage 82
  • MLS Status Active
  • Other Amenities Golf, Waterfront
  • Zoning R-1

Very special land parcel. Western views overlooking Highland Lake. Pastures, fields, stone walls, brook & wooded areas showcase this wonderful building site. Ideal single family or subdivision potential. Land is actual several parcels on both Spencer Hill Rd and Spencer St totaling 81 +/- acres, Sewer & water nearby, but not yet permitted.

Listing Courtesy of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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804 East Wakefield Boulevard Winchester CT 06098

MLS Number 170424516

  • Single Family
  • Acreage 0.17
  • Square Feet 2,492
  • Bedrooms 3
  • Bathroom 3

Do you love watching magnificent sunsets over the lake? You can choose your haven at this beautiful lake front home! From the Brazilian hardwood stationary dock or three tiered patio with sun setter canopy and covered dining or inside by a cozy fire or maybe just relaxing on the balcony off the master bedroom. Set in a quiet cove on the east side of Highland Lake this 2400 sf colonial has so much to offer. The great room and dining room combo has huge windows to give you the most beautiful view of the lake, a lovely washed brick fireplace & gorgeous hardwood floors. The updated kitchen features Corian counters and Hickory cabinets. A bedroom and full bath finish the main floor. The second-floor offers two more bedrooms with new hardwood floors & cathedral ceilings. The breathtaking master bedroom has as much glass that the home designer allowed & a full length glass walled balcony. The guest bedroom can fit a whole crew of folks. For your entertaining pleasure the walk out basement offers a 25x16 tiled room with a refrigerator, sink, cabinetry and a 1/2 bath with laundry. Outside you'll find a hard covered dining area open to the 3 tiered patio with bluestone stairs right to the water. The stunning stationary dock has hardwired lights, under-dock lighting, a concrete pillar and pad, and is constructed with steel beams for years and years of enjoyment. All 4 seasons are beautiful on the lake, even winter, watching cross-country skiers glide across the lake.

Listing Courtesy of William Raveis Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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760 Lake Drive Winchester CT 06098

Winchester, CT760 Lake Drive

Price$735,000

Est. Mortgage: $/month

MLS Number 170414426

  • Single Family
  • Acreage 0.12
  • Square Feet 838
  • Bedrooms 3
  • Bathroom 3

**Exciting direct waterfront property! This is your escape to paradise! Highland Lake is approx.2 hrs. from NYC or Boston, minutes to Rt 8 and close to all the restaurants, wine trails and breweries Litchfield County has to offer. This exquisite home was entirely rebuilt in 2012! Enjoy lots of beautiful sunsets, sun filled rooms, 3 fireplaces and all the accoutrements of lakeside living. This home has it all! Three bedrooms, 3 bathrooms, and a great room with beautiful vaulted ceilings and many windows, allowing natural light to fill your home. The beautiful view from your trex decks and dock will inspire you! Beautiful open living and kitchen area with all the appliances and work space any chef would want. Lovely master bedroom with gas fireplace vaulted ceiling, hardwood floors and walk in closet. This is a home or hideaway for every season! Pay for your own vacation home with weekly rentals at $3000 or nightly at $400 as current owner has been doing!! Town hall square footage does not include finished upper story.

Listing Courtesy of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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107 West Wakefield Boulevard Winchester CT 06098

MLS Number 170357239

  • Single Family
  • Acreage 0.23
  • Square Feet 2,392
  • Bedrooms 3
  • Bathroom 3

Highland Lake - Waterfront with panoramic views. Enjoy the benefits of direct waterfront without the high taxes! Beautiful updated lake home with 2,392 square feet, 3 bedrooms and 3 full baths. This home features a stylish gourmet kitchen with granite counters, center island and stainless steel appliances, spacious dining room with pellet stove and a large lake facing living room with gas fireplace and dual sliders that open up to the front deck for breathtaking views! Don't miss the master bedroom with spa-like shower, sitting area, cathedral ceiling, sky lights, walk-in closet and sliders to deck. Other special features include: outdoor BBQ area with views, 2 car garage, ample off street parking, public water and sewer. One step into this home and you'll appreciate the attention to detail and the quality improvements; including the tankless hot water heater, roof, windows, central air, furnace, decks and so much more! Easy walk to the beach. One of the best locations to watch the sunrise! Highland Lake is one of CT's cleanest lakes and offers all-season activities. Easy 45 minute drive to Hartford, Bradley International Airport and 2.5 hours to NYC

Listing Courtesy of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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401 West Wakefield Boulevard Winchester CT 06098

MLS Number 170386449

  • Single Family
  • Acreage 0.75
  • Square Feet 2,050
  • Bedrooms 3
  • Bathroom 2

Perched over the beginning of Third Bay, this home sits across the street from the water yet offers some spectacular all season views over Highland Lake while maintaining affordable taxes. Included in the sale is a waterfront parcel that contains 200' of direct waterfront with a modest size cabana used for storage in the winter and entertaining in the summer. The contemporary style home features 3 bedrooms and 2 full baths. Enter the home from the large wraparound deck overlooking the lake into the large family room that contains a nice dining area, breakfast bar and wood stove for cozy winter nights, there is lots of glass affording great lake views. French doors lead you into the remodeled kitchen and from there you can enter the living room with a fireplace and propane log set, another set of french doors lead you into a bedroom overlooking the lake. On the upper level there is a full bath and two modest size bedrooms. This home has much to offer and is great for entertaining from a very intimate to the largest of gatherings.

Listing Courtesy of Northwest CT Realty

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$
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$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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444 Platt Hill Road Winchester CT 06098

Winchester, CT444 Platt Hill Road

Price$625,000

Est. Mortgage: $/month

MLS Number 170438675

  • Single Family
  • Square Feet 2,764
  • Acreage 4.99
  • Property Style Ranch
  • Bathroom 2

Outstanding and Well Maintained One Owner Residence tucked away on 4.99 Acres. Spacious Ranch with Contemporary Flair makes for Easy and Relaxed Country Living. Attractive Eat-In Kitchen with separate Walk-in Pantry Closet. Private Formal Dining Room. Awesome 30' x 20' Great Room / Family Room accented by Cathedral Ceilings, Hardwood Floor and Custom Stone Fireplace. Master Suite includes 2 Walk-in Closets, Generous Size Master Bath. 20' x 13' Upper Loft overlooks Family Room - Ideal as Computer Room / Study. Beautifully Landscaped Grounds enhanced with Front Entry Brick Paver Walkway & Steps, Perimeter of Yard Offers Wild Raspberry & Blackberry Bushes. Above Ground Pool. Fire-Pit, Extensive Decking with "Sun Setter" Awning. Unique Heating System Fueled by ones choice of Oil, Wood or Coal. 8 Year Old Hybrid Electric Hot Water Heater. Central Air, Generator Ready. Attached "Clean" 3-Bay Clear- Span Garage with Electric Door Openers. 2,400 +/- Square Foot Basement has both Walk-out and Drive-In Doors. Good Safe & Dry Space for Extra Storage. Perfect Location for either Year Round or Weekender Living. Just to Name a Few there are Recreation Venues Galore: Platt Hill State Park, Burr Pond State Park, Highland Lake, West Hill Lake, Ski Sundown along with a convenient drive to the "Berkshires". Great Private Rural Location, yet all Major Shopping needs and services are in Close Proximity. Move-In Ready!

Listing Courtesy of Cohen Agency

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$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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834 East Wakefield Boulevard Winchester CT 06098
Pending Continue to Show

MLS Number 170431025

  • Single Family
  • Square Feet 1,452
  • Acreage 0.05
  • Year Built 1990
  • Bathroom 2

Breathtaking views from this wonderful waterfront on Highland Lake. This listing won't last long! Spacious kitchen and dining area with a pretty tiled floor, newer kitchen appliances and great views of the lake!! The living room is carpeted and also has views of the lake. Off the living room area you will find the laundry room/utility room. A half bath completes the first floor. The second floor consists of two bedrooms and a spacious full bath. There is a balcony deck on the second floor to take in the serene views of the lake. Absolutely fabulous entertaining area with multiple Trex decks, a nice wide dock and concrete stairs into the lake making it easy to swim, float, kayak, paddleboard. This cottage also includes 833 East Wakefield Blvd. consisting of 0.24 acre lot across the street. Highland Lake is a 444 acre lake and noted for its clean water and trophy fishing. The lake is three miles long and 7 miles around and consists of three bays. A beautiful lake all four seasons! Along the shoreline of Highland Lake you will find stunning year round homes and summer residences. Approx. 15 minutes to Litchfield Village, 30 min. to Bradley International Airport, 2 Hrs. to NY and Boston. Music venues, wineries, breweries, shopping, great restaurants, parks, hiking trails all nearby. Note: Taxes on MLS reflect the cottage at 834 East Wakefield. The taxes on the lot across the street 833 East Wakefield are $126.78. (Two field cards 834 East Wakefield and 833 East Wakefield).

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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870 West Wakefield Boulevard Winchester CT 06098
Pending Continue to Show

MLS Number 170429416

  • Single Family
  • Acreage 0.12
  • Square Feet 1,682
  • Bedrooms 2
  • Bathroom 1

Come see....It's a perfect getaway! Highland Lake waterfront year round ranch cottage located at the east end of 3rd bay. Open floor plan for one level living or expand the lower unfinished level w/plumbing in for future bath. Lower level walk out basement leads to a beautiful stone patio and a sandy area to waters edge with concrete steps into the water. No lawn to mow here. You & your family will love playing in this sandy area. Close to Rt8, restaurants, breweries, shopping and all Litchfield County has to offer. 30 min drive to Bradley Airport and 2 1/2 hours to NYC

Listing Courtesy of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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121 West Wakefield Boulevard Winchester CT 06098

MLS Number 170399855

  • Single Family
  • Acreage 1
  • Square Feet 2,265
  • Bedrooms 4
  • Bathroom 4

This impressive colonial was designed in 1996 and sits at a higher elevation than most homes on Highland Lake. The property stands tall on a 1 acre lot and is generously sized with 4 bedrooms, 3.5 baths and an in-law apartment off of the kitchen. TONS of space and potential with the full basement and the 2 car garage. You can relax by fire pit in the backyard, the fireplace in the living room or move the jacuzzi on the back deck! Stunning views from the master bedroom's glass enclosed deck - a beautiful place to wake up in the morning. Walk down the hill, set your feet in the lake on your new dock and call Highland Lake “Home”. Agent/Owner related.

Listing Courtesy of Berkshire Hathaway NE Prop.

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$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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17 Woodland Avenue Winchester CT 06098

Winchester, CT17 Woodland Avenue

Price$399,900

Est. Mortgage: $/month

Open House

MLS Number 170425462

  • Single Family
  • Next Open House: Sun 09/26 12:00 pm. to 3:00 pm.
  • Square Feet 1,980
  • Acreage 0.38
  • Property Style Colonial

This home is like living in your own private oasis within walking distance to Highland Lake. Relaxing staycation says it all! Beautiful landscaping and fountains sprinkled throughout the fenced in yard. You can also sit on the patio and hear the waterfall coming off the spillways of the lake. Once you step inside you will find a chef's grade kitchen with commercial oven range, subzero refrigerator, dishwasher, granite counters and a large island. The family style dining room features a bar area with a new beverage cooler and a kegerator. It is also anchored by a working antique cooking stove that burns wood and creates tons of heat. Right around the corner there is a large fireplaced living room with wood floors and built-ins. The 2nd floor features 3 bedrooms, a full bath and a common area that will double as an office or a home school. There is a sewing/craft/flex room located up a short staircase off the master bedroom. This home is sure to please everyone and entertaining is a snap. No detail has been left undone.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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110 Roberts Avenue Winchester CT 06098

MLS Number 170428996

  • Single Family
  • Square Feet 2,476
  • Acreage 2.54
  • Year Built 1954
  • Bedrooms 4

Welcome to this 2,845 sq ft colonial style home on 2.54 acres lot. This home features new windows, new well pump and newer roof. Situated in a park like setting is a pristine 20 by 40 inground pool and large outdoor fireplace. Enjoy those wonderful new England evenings from your screened in porch with flagstone flooring. The patio opens to a large plant room/laundry room with skylights and a full bath. Formal living room with a fireplace, hardwood floors and custom shelving. Large great room with wood flooring, fireplace, a skylight and solid wood paneling complete with a custom bookcase. Off the great room is a bedroom with a built-in desk. The great room opens to a kitchen nook. Large kitchen with built-in ovens with plenty of cabinet storage and a skylight bringing in natural light! Formal dining room with a custom bar and gorgeous slate flooring. Upstairs includes two bedrooms and the master bedroom with a full bath, a walk-in cedar closet, and two other closets/storage. New carpet was installed all upstairs including stairways. There's a nook for the office/sitting area on top of the stairway. A partial finished basement with dry bar, and workroom awaits the person who is handy to update a third bathroom. Room to park your RV or Boat with a circular drive! Just minutes from town, Highland Lake Rt 8 and Rt 44. Absolutely perfect for entertaining inside or outside. This one owner home was well maintained and loved.

Listing Courtesy of www.EntryOnly.com

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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113 Hollow Hill Road Winchester CT 06098

MLS Number 170431335

  • Single Family
  • Acreage 2.33
  • Square Feet 1,872
  • Bedrooms 2
  • Bathroom 2

PRIVACY IN WINCHESTER CENTER - Tucked away off of peaceful Hollow Hill amidst stone walls in a classic New England setting, you'll find this well kept one owner Colonial with a unique, versatile layout. The 240 sq ft heated recreation room, which is not included on the town assessor's tax card, brings the total square footage to 2,112. An interior balcony, a Den that could serve as a Guest Room or 3rd Bedroom, a spacious Rec Room, a brick hearth fireplace - there is a lot to enjoy here. Minutes from kayaking and fishing at Park Pond or Winchester Lake, power boating and the town beach at Highland Lake, and all of the outdoor recreation available in the Litchfield Hills, this is an ideal location to enjoy all that the area offers. Winsted's Gilson Theatre, The Infinity Theatre and the Yale Summer Music series in Norfolk, farm to table restaurants throughout the region are just the beginning. Come see for yourself!

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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